Triethylamine → N4-{3-Fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidine-2,4-diamine

HRID 2192182Notes

Reaction equation

HRID 2192182 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][CH:24]=[C:25]([CH3:26])[C:18]=34)=[C:12]([F:27])[CH:11]=2)[CH:3]=1.C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[F:27][C:12]1[CH:11]=[C:10]([NH:9][C:4]2[CH:3]=[CH:2][N:7]=[C:6]([NH2:8])[N:5]=2)[CH:15]=[CH:14][C:13]=1[O:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[NH:23][CH:24]=[C:25]([CH3:26])[C:18]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 116609846-Chloro-N4-{3-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidine-2,4-diamineHCID 178418361HCID 178418361, compound

Product 1

HCID 11523150N4-{3-Fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

50 mg (0.13 mmol) of 6-chloro-N4-{3-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidine-2,4-diamine are dissolved in 10 ml of ethanol. 36 μl (0.26 mmol) of triethylamine and 28 mg (0.03 mmol) of 10% palladium-on-carbon are added, and the mixture is hydrogenated under atmospheric pressure in a hydrogen atmosphere overnight. The mixture is then filtered through Celite®, and the celite is washed with methanol. The solvent is removed under reduced pressure and the crude product is purified by preparative HPLC.

Workup

  1. filtrationThe mixture is then filtered through Celite®
  2. washthe celite is washed with methanol
  3. customThe solvent is removed under reduced pressure
  4. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-2b25b9687ca04bff85f40a2a0352425c
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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